🛡️ Licensed in IL · TX · OH · IA · SC · MI

Trucking Insurance
Built for Owner-Operators
& Fleets

Whether you run one truck or a full fleet, Legacy Shift Insurance Agency gets you covered through the top commercial carriers — fast, personalized, and stress-free.

Authorized Carriers GEICO Progressive + More
Alexandra Sokolenko — Legacy Shift Insurance

🚛 DTC Student? Mention Dispatch Training Center for priority service — call 224-600-3200 for a same-day consultation.

We Represent the Best.
You Get the Options.

We work with America's top commercial carriers so you get competitive pricing, real coverage, and an agent who knows trucking inside and out.

GEICO Truck Insurance
GEICO Truck Insurance
Competitive rates for semi-trucks, owner-operators, and fleets. Strong liability, physical damage, and cargo coverage backed by a top-rated carrier.
Get GEICO Quote →
GEICO Commercial Auto Insurance
GEICO Commercial Auto
Covering vans, work trucks, delivery vehicles, and mixed fleets. GEICO's commercial auto program offers flexible options for every business vehicle.
Get Quote →
Progressive Commercial — Put Your Trust in #1
Progressive Commercial
America's #1 commercial auto insurer. Covers everything from one truck to a 50-unit fleet — with flexible payments and dedicated commercial expertise.
Get Progressive Quote →
Amwins Access — Specialty Trucking Insurance
Amwins Specialty Trucking
For hard-to-place risks and non-standard fleets. Amwins opens doors standard carriers won't — specialty and surplus lines coverage built for unique trucking operations.
Get Amwins Quote →

Every Coverage Type Your
Trucking Business Needs

From your first truck to a 50-truck fleet — fully covered.

🚛
Primary Liability
Required by the FMCSA for all commercial carriers. We make sure you're compliant and protected from day one.
📦
Cargo Insurance
Protect the freight you're hauling. Covers loss, theft, and damage to cargo in transit.
🔧
Physical Damage
Comprehensive and collision coverage for your truck and trailer — your biggest assets on the road.
🛡️
General Liability
Covers third-party bodily injury and property damage that occurs during business operations.
👷
Workers Compensation
Protect your drivers and employees in case of on-the-job injuries. Required in most states.
🏢
Business Owners Policy
Bundle general liability and commercial property into one smart policy for your business.

Why Trucking Professionals Choose Us

We speak trucking. We know dispatch. And we shop multiple carriers to find you the best rate.

🏆
Top
Carrier Access
GEICO, Progressive, Amwins & more — we shop multiple carriers to find your best rate and coverage.
Same Day
Quote Turnaround
Submit your info and we'll have a quote back to you the same day. No waiting.
🚛
1–50+
Trucks Covered
Owner-operator or full fleet — we scale with your business at every stage.
🤝
Real
Personal Service
You call us directly — no 1-800 numbers, no bots. Real agents who know your business.

Get Your Trucking Insurance Quote Today

Fill out the form and our team will contact you within hours with a personalized quote.

Or call directly: 224-600-3200 · We respond same day

What Our Clients Say

★★★★★

"Alexandra took the time to explain every option available. The process was professional and she made sure we had the right coverage for our operation."

Nadzeya Andreichuk
Pennsylvania
★★★★★

"Simple, professional, and stress-free. Alexandra got me the right trucking coverage quickly and at a better rate than I had before."

Miras Orynbayev
Illinois
★★★★★

"Knowledgeable, responsive, and professional. She found me a better rate than I had before. I highly recommend Legacy Shift to any owner-operator."

Ivan Tsakhniy
Illinois
★★★★★

"I called on a Friday and had my policy in place by Monday morning. Victoria walked me through everything step by step — best experience I've had with an insurance agent."

Dmitri Kovalenko
Texas
★★★★★

"As a new owner-operator I didn't know where to start. Liliana was patient, explained everything clearly, and got me covered at a price I could actually afford. Highly recommend."

Marcus Johnson
Ohio
★★★★★

"Switched from my old broker and saved over $200 a month on the same coverage. Legacy Shift actually shops around for you instead of just selling you the first thing they find."

Sergiy Bondarenko
Michigan
★★★★★

"I run a small fleet of 4 trucks and these ladies handle all our policies. Always responsive, always professional. I don't have to worry about insurance anymore — that's priceless."

Raul Espinoza
Iowa
★★★★★

"My previous agent took a week to return calls. Alexandra picks up the phone same day. When you're running freight, that kind of service matters more than anything."

Taras Petrenko
South Carolina
★★★★★

"Victoria helped me get cargo and liability coverage sorted out in one call. No back and forth, no confusion — she knew exactly what I needed and made it happen fast."

Olena Marchuk
Illinois
★★★★★

"I've been trucking for 12 years and dealt with a lot of agents. Legacy Shift is the first one that actually felt like they were on my side. Got me better coverage and a lower premium — can't ask for more than that."

Brian Mitchell
Texas

Licensed Professionals Ready to Help

Call any agent directly — real people, not bots, who understand your trucking business.

Alexandra Sokolenko
Alexandra Sokolenko
Agency Owner
Life · Health · Property · Casualty · Commercial · Trucking
📞 224-600-3200
Victoria Tsakhniy
Victoria Tsakhniy
Licensed Producer
Life · Health · Property · Casualty
📞 224-829-1332
Liliana Matcas
Liliana Matcas
Licensed Producer
Life · Health · Property · Casualty
📞 312-439-2526
Alexandra Sokolenko

I Built This Agency for the Trucking Community

After years of working with owner-operators and dispatchers, I kept seeing the same problem: trucking professionals overpaying for coverage — or worse, underinsured when it mattered most.

Legacy Shift Insurance Agency was built specifically to serve the trucking and transportation community. We represent GEICO, Progressive Commercial, and Amwins — giving us access to both standard and specialty markets so we can find the right fit for every operation.

When you work with us, you're not calling an 800 number. You're calling a real agent who understands your routes, your risks, and your business.

Licensed in IL · TX · OH · IA · SC · MI GEICO Appointed Progressive Commercial Amwins Specialty Lines Trucking Specialist

Ready to Protect Your Trucks?

Get a free quote today — same-day response, no pressure, just honest insurance advice from people who know trucking.

Get My Free Quote → 📞 Call 224-600-3200